Jiriaya's latest student
by Jiraiya316Says
Summary: Whilst subtlety was something that jiraiya could do, he much preffered doing things directly. When he meets the last Uchiha, he sets off a plan that will change Sasuke's outlook on life far more than anyone else in the village that had tried before. Mature themes Non Yaoi.


_I'm not good enough! _Sasuke internally shouted as he looked frustratingly at the headband in front of him.

The thoughts that the Uchiha clan heir was having, were not common for one of who had achieved what he had just achieved. He had just graduated from the ninja academy and he was now a genin! On top of that, he placed top of his class and was named as the best among his peer group.

One would normally be happy with that however Sasuke Uchiha was not. His standards weren't the same as the normal person. He wanted, no needed to become far greater than that! Considering the goals he had, and what he measured himself against, Sasuke knew that he was only just at the beginning.

As he was walking down the street, with the trademark scowl, Sasuke was so deeply lost in his thoughts, the genin didn't realise that he was walking directly into someone. That someone happened to be perched precariously against a fence, almost as if he was peeping inside of it.

Jiraiya, hadn't been paying all that attention to the outside world. He was busy gathering information for his next story. That was until someone rude individual bumped into him. Turning around he noticed who it was. In a shinobi village, it was impossible to not who was in front of him. He had heard everything from sensei regarding the boy and knew that if something wasn't done, there was a very high possibility that Sasuke would go down the same path that his once team mate did.

_Can't let that happen to the Sharingan._

_Sarutobi would kill me if he knew I did nothing._

_The Gaki has a lot of female followers. I bet if I just show him the way of the feminine body, he won't be as focused on killing Itachi. This could work out really well._

Jiraiya was never one to do things subtlety. A plan as good as anything else that he had come up with in the past, Jiraiya went into action. Without warning, Jiraiya roughly grabbed the back of the Uchiha's skull and pressed it up quickly against the wall with his eyes lined directly up with the holes.

Without having time to even close his eyes for fear of impact with the fence, Sasuke could only stare. Gawk at the sight of mature kunoichi who were bathing in the hot springs utterly naked. It was very much a different sight to the girls at the academy who annoyed the shit out of him.

Sasuke stared for a good 20 seconds before realising what he was doing and that it wasn't with his consent. Taking his head from the wall, there was a significant blush on his face. "What the hell was that for and who the hell are you!?" Sasuke whispered / yelled at the man.

All he got in response was a "Come with me" before a hand was placed on his shoulder. A shunshin occurred as Jiraiya teleported the two of them away.

_Yes… Kushina said that I couldn't corrupt her little boy but Mikoto never said anything like that._

"Don't make me repeat myself, who the hell are you!?" Sasuke voiced with increasing frustration. He actually had a rough idea in his head due to academy textbooks but he wanted to make sure.

With utter glee, Jiraiya created a plume of smoke, masking Sasuke's vision. When it cleared, the man was standing on top of a large toad. "The Legendary Ninja, Jiraiya the Gallant!"

A deadpan look was all that Jiraiya got and it was quickly morphing into a scowl. The only thing that was keeping the uchiha their was the fact that this man was probably the only person outside of the hokage that could beat his older brother. _If he could teach me, then finally I can get the power to kill Itachi._

"Can you teach me! I have to become stronger!" Sasuke pleaded with the legendary ninja. It was rare that you even got the opportunity to talk to such a strong ninja, let alone get the chance to train with one! He had to make this count!

Jiraiya dismissed the Toad although he didn't dismiss the request. Instead he put his hand up on his chin in a thinking pose."What's in it for me? Why should I train you kid? What have you got to offer? What makes you so special?"

Admittedly Sasuke didn't expect to get this far. "Umm, because I graduated rookie of the year, everyone tells me I'm a prodigy, that way you won't have to waste much time teaching me." The Uchiha heir had never really had to sell himself and it showed.

"Been there, done that. Trained the best prodigy the world has ever seen. Think of something else you can offer me." Jiraiya instantly rebutted what he had to say without any care whatsoever.

Put on the spot and having to think, Sasuke came up with another suggestion "The Uchiha clan has a lot of money! I can pay you!?" Sasuke asked, hoping that that was good enough.

It wasn't.

"I'm rich kiddo, I have enough money that I can buy whatever I want. Think of something else." The sannin fired back quickly, putting all the pressure on sasuke yet again.

Racking his brain, the black haired boy tried to think of something that he could use to his advantage. It was then he remembered what had happened just before they appeared in the training ground. "I can help you with peeping at the women. You were writing information down right? I can use my sharingan to help give you information that you could use."

It was a long shot and Sasuke doubted that it would work but he was running out of ideas. Much to his surprise, Jiraiya paid him the most amount of attention so far. He must have struck a chord.

_Brat can use his sharingan to commit their perfect bodies to memory. Kid's a gold mine!_

"Well can you activate your Sharingan?" Jiraiya questioned which made Sasuke deflate. The answer was all over his body language.

"I'm sure someone of your stature as a great shinobi would be able to help me unlock it. That way I can help you."

Jiraiya knew that he was going to help the boy, he just wanted to make the brat work for it. "I suppose I could do that but if I do agree to help you, I am going to ask for you to commit to 3 things that I want in return."

Latching on when he saw a hook, Sasuke was desperate! "Anything, I'll help you with anything as long as you help train me to give me the power I need."

An eyebrow rose. "Anything you say. Will you be willing to commit to that via a seal? Without knowing what my conditions are?"

That gave Sasuke pause for a moment as he contemplated his options. In the end though, the clear message running through his mind was that the man in front of him was the same person that taught the legendary fourth Hokage. If he could teach him to that same level, then anything would be worth it! "What are the three conditions?"

_Kids got balls. _"I'm not going to tell you. You're just going to have to trust me that its going to be something that you accept because you won't like the punishment. I will say though, that in my opinion, I think you will like these conditions whether you know it or not."

There was a moment of deliberation. The lure of power though was simply too much for the newly promoted genin. "Sign me up! I'll do whatever it takes. I need to avenge my clan."

_I've always wondered what it would be like to train someone with a bloodline limit._

"Okay first thing, and this is not one of the three conditions, however, if you mention to anyone as to who is training you, I'll remotely seal off your chakra, permanently." That was a very serious threat and one that Sasuke Uchiha couldn't help but gulp at. He dumbly nodded.

"You're not good enough yet to have my reputation on the line for teaching you. Stop being shit before you can proclaim who it was that taught you." Sasuke gritted his teeth and stared with fire in his eyes at the man in front of him. As much as he didn't like hearing that he was weak, it was a breath of fresh air compared to everyone saying how great he was.

_Good, that will give him a bit of added motivation. I just don't want the other conditions to come back to me._

"First condition is that we get your sharingan and then you help me with my research." the word "research" was not lost on Sasuke. "I write books, of the erotic kind. You will be my beta reader." Jiraiya was testing Sasuke on his resolve, and judging by the massive blush on his face, it was definitely going to be tested.

"For you to do this properly, you are going to have to have a lot of experience with women."

There was an insinuation there that Sasuke didn't like. He had never bother thinking about girls that way! "What do you mean!? All of the girls at the academy fawned over me. I have plenty of experience with girls!" Sasuke replied hotly, all whilst a blush appeared on his face.

"And what did you do with that? Did you kiss any girls, make out with them, see anything?" _Wow this guy is a massive freaking pervert!_

"No…" Sasuke mumbled. He definitely wasn't going to tell the man that Naruto of all people kissed him earlier in the day.

"Well then how are you going to be able to tell if the stories are good or not if you have no experience? Face it kid, you're going to have use those good looks of yours if you want to get my help." The insinuation was not lost on Sasuke and he merely blushed. Whilst he was cool, calm and collected, the large majority of the time, that was in things that he had experience. Sasuke had no experience in this stuff and it showed.

"What's the next condition?" Sasuke grunted out, hoping to move this conversation along.

"Well I'm all for helping the village by teaching the younger generations but you see there is a problem. That problem is that I am lazy. Therefore, you're also going to be forced to teach your team mates." there was a look of shock and indignation on the face of Sasuke. For someone who was so introverted and anti social, this went completely against who he was as a person.

"What!?" Was all that Sasuke could reply with.

"Here me out on this one kid. The biggest problem that you have as an Uchiha, especially when you get your sharingan, is that you are shit at explaining techniques due to simply copying a jutsu and then moving onto the next one.

By teaching something to multiple different people, it forces you to change your wording and adjust how you think about the technique, giving you a far greater understanding of the technique.

"But what if my team mates are so terrible they don't get it?"

"Sasuke, the signs of a great shinobi isn't how strong they are themselves. It's how strong they can make the people around them. I'll give you a hint about becoming a chunin, 9 times out of ten, the reason why genin fail the chunin exams is to due mentality rather than their skills.

You're going to have to lead teams in the future if you ever hope on getting past genin let alone trying to become a great leader like Fugaku." Shock was evident on Sasuke's face as he registered what had just been said.

It was a commonly known thing around Konoha that you don't mention Sasuke's family to the lone survivor. It was taboo.

This meant that when Sasuke heard it, it packed a lot more of a punch and made whatever comment came with it. "How are you going to rebuild your clan into the famed and feared Uchiha clan if you can't even lead a team of genin on a mission? Teaching is a critical part of being a leader and its something you're going to have to learn if you ever want to become a competent leader, which is something completely different from being a good shinobi."

Jiraiya lectured the boy which resonated with him. All this time, he had focused on becoming strong enough to defeat Itachi, that he had never even thought about the steps that it would take to rebuild his clan.

"Fine… you're right. I'll help whoever my team mates are. I won't like it however." Sasuke admitted. Which wasn't easy for the teenager.

"You may not like it but these skills will make you a better shinobi. Now onto the final one. This one is a personal one for me, not just one that will push you to become a better shinobi." The change in tone when Jiraiya spoke was clear and evident to Sasuke. He could tell that this was the most important condition by far.

"Protect Naruto Uzumaki."

Out of all that Sasuke expected, that was not one of them. "What!? Why? Why him of all people?"

"Because he is the one person that needs it and the one person that will help you the most in terms of becoming a shinobi worthy of killing Itachi." if mentioning Fugaku was taboo around Sasuke, mentioning Itachi was much worse. You had to tread very carefully. Jiraiya didn't simply due to the shear difference in power.

"Naruto is someone who has had a similar upbringing to yours. One of hardship that no child should have to go through. Whereas you had a support network of health professionals looking into your mental state right after the incident and you also had the funds of your clan to support you, Naruto hasn't."

Through gritted teeth, Sasuke replied. "How do you know all of this?" trying to ignore the comments being made. It brought up painful memories.

"I am the man in charge of intelligence for the village. There is very little I don't know. Now back to the main point, where you had a support network, if you wanted it, Naruto did not. So many people that he doesn't even know have failed him. Teacher's kicked him out of class, those that should have given him care and a foster family were too busy being selfish and looking after a child in desperate need of assistance.

Don't let the failures continue Sasuke please, for this old man. Please take care of Naruto. He looks up to you and idolizes you like a brother. You don't have to like him, you don't have to be friends with him but please look after and protect him." it was the most emotion he had seen out of the man since they had been talking and if he was honest with himself, he didn't hate Naruto. He just thought he was annoying.

The look he had seen in Naruto's eyes, the same one which he was confident that Naruto had seen in his, was one that you didn't get as a kid unless you had been through some traumatic experiences. The problem was that he was annoying.

"Why are you so fixated on Naruto? And you mentioned that he would be able to help me into a stronger shinobi, how?"

"That's a story for another time Sasuke. Now onto how he can help you become a better shinobi… You may not have noticed it, but Naruto is incredibly talented. You may not see it. He definitely hasn't seen it yet but trust me on this. If there is one person that can push you, if given the chance, it is Naruto. Just see if you have doubts in six months, after seeing how much he progresses, due to you helping him."

That was a lot of pressure to place on a genin and Sasuke was feeling uncomfortable. "So that's a lot to take in I know, but if you want my help, that's what its gonna cost." Jiraiya hoped that Sasuke took this, he really did. It would be very beneficial to both Sasuke and Naruto and he tiered it in a way that he he hoped would make the Uchiha child develop bonds to the village.

With resolution set in stone, Sasuke replied. "Yes. I'll do it."

The mood changed after the black haired boy said this and it lifted considerably. "Nice one brat! Now it's time to get those bullshit overpowered eyes of yours to start working for once." Sasuke was irked by the comment.

With that said, Jiraiya charged at Sasuke. It wasn't slow either. Sasuke's eyes opened wide and before he knew it, there was a significant amount of pain in his gut. Jiraiya had kicked him hard, launching several feet back.

"They say, all it takes is one good fight to activate the sharingan._" _Jiraiya wasn't goign to mention that it required to go to edges of life and death but as they always say, don't ruin a good story with the truth.

A fight sounded pretty good to Sasuke. He rarely got the chance to test himself against those stronger. A smirk appeared on his face as he went through some hand seals. "Fire Release: Grand Fireball Jutsu!" Sasuke called out before breathing deep into his lungs and launching the largest fireball he could make. He watched as it raced towards his enemy and looked as if it connected dead on.

"Not bad kid, sucks that your shit though." A voiced called out from behind as sasuke once again got rocked. This time it was a punch to the face that was powerful enough to draw blood. _He's definitely not holding back _Sasuke told himself and he grinned despite the immense amount of pain he was in.

"Now let me show you a real fire jutsu." Jiraiya continued, not releasing the name of the jutsu. Multiple fireballs, each the same size of the one that Sasuke created. In addition to being the same size, they moved far quicker.

Eyes went wide as he could feel the heat coming off them. Sasuke knew that he couldn't let them hit! As fast as he could, Sasuke leapt out of the way. "Ahh he called out. His foot got hit with the last fireball. He couldn't jump out of the way quick enough.

Rolling around on the ground, Sasuke focused on putting out the fire that was on his sandal. He didn't notice the kunai coming that sliced through his pants and cleanly went through the side of his leg. Following up this, a shuriken embedded itself into his other leg.

"Ahh!" Sasuke called out, clearly in pain but also frustration. He couldn't even catch a break let alone hope to amount any sort of offensive attack now that Jiraiya was taking him seriously.

_Is this the difference between me and a strong shinobi? _Sasuke asked himself. Outside of Itachi, this was the first time he was scared about a fight. Jiraiya wasn't pulling punches at Sasuke didn't know was that this was the difference between a genin and a high level chunin.

Sasuke didn't even have time to pull the shuriken out of his leg as he looked up, something catching his eye. He wasn't entirely what the name of it was, but going by the looks, it was a sphere of raw chakra coming directly towards his face. Eyes widened palpably _He hasn't pulled any punches yet. If I don't move that's going to hit me!_

A surge of adrenaline rushed through Sasuke followed shortly after by a surge of chakra that rushed to his eye sockets. Obsidian black pupils mutated and morphed colour, adding a red tinge, with a single black tomoe appearing in each eye.

Without knowing what he was doing, Sasuke watched as it seemed to slow down the pace of the jutsu, Due to the adrenaline rushing through his body, Sasuke launched himself to the side, not seeing the grin that was on the face of Jiraiya, solely focused on making sure that he didn't die.

And then, right in the middle of it, the fight and also the suffocating aura that was surrounding Sasuke vanished into nothingness. "Why'd you stop?" Sasuke couldn't help but ask as he slowly got up from the ground, then pulling the shuriken out of his leg.

"Hold a shuriken up to your eyes brat and see the reflection kiddo." Jiraiya replied and Sasuke didn't need to be told twice. There was an odd sense of glee. The Uchiha clan heir was not proud of the fact that, a right of passage in his clan, took so much longer for Sasuke to achieve than his older brother Itachi. If there was one thing that Sasuke had an insecurity about, it was either internal or external comparisons to Itachi.

With a sense of hope, Sasuke looked into the shuriken and could clearly make out that that there was a colour change in his eyes. The shuriken wasn't the most reflective surface but it did the job. It allowed Sasuke to see the change, including the one tomoe in each eye which was all he needed.

"Yes…" the black haired boy was not normally one to get excited but even an event as monumental as this, was something that he couldn't hold back. A fist pump went along with it.

Jiraiya walked over to the boy and placed his hands loosely over the stab wound from the shuriken. Sasuke had momentarily forgotten about the injury during the heat of the battle and finding out he had his sharingan activated but now that the adrenaline was wearing off, he noticed it significantly.

Due to decades spent around the best medic that Konoha had created, Jiraiya was able to use heal Sasuke enough so that the cut was sealed over and it was no longer bleeding.

"Now brat." The glee that was in Sasuke's eyes diminished slighly, hearing the term. "Channel chakra into your eyes, even more so than you are doing now. Don't rush into it but slowly feed chakra to get a better feeling for it."

The Uchiha clan heir did just as he was instructed and suddenly, he could feel the _difference_ in how his eyes felt. It was as if there was a mind muscle connection to his eyes through chakra that never existed before.

"Now, slowly, reduce the chakra to even less than before. You want to turn off your sharingan."

"What? Why?" Due to seeing that the elder shinobi was trying to help him and had most importantly actually executed on helping him, there was no confrontation in the tone of his voice, or malice.

"Because you want to get good at being able to turn them on at will, whilst maximizing your chakra efficiency when using them. You want to be able to turn them on next time on your command, not having to get schooled in a fight beforehand."

_That makes sense. _Sasuke thought to himself and did what he was told.

For the next ten minutes, Sasuke practised, cutting off the chakra to his eyes, thus turning off the sharingan, waiting a few seconds and then turning back on.

"Now kiddo, its time to make this deal official. We'll go back to your place and right the terms into a seal and then I will tattoo onto your body." Sasuke was hesitant but he knew that he had agreed to this. This man in front of him was not afraid to pull punches as evident and Sasuke questioned if even having the sharingan now would do much at all to save himself.

Going back to Sasuke's house, Jiraiya prepared everything. "Take off your shirt Gaki and lay down stomach first. This is going to take a while." Jiraiya commanded to which Sasuke obliged.

"If this is going to be permanent, can you at least make it not look like a seal, can you somehow cover it up? Like a tattoo?" Sasuke requested. He hated the idea of having a brand on him, that if people saw it, they would realise what's up.

"Yeah sure, I've done quite a lot tattooing, due to seals, this isn't my first rodeo. I could do a simple Uchiha Fan or I could do something far more in depth, like something that you can have to honour your clan?"

"I'd prefer the last one if possible." Sasuke didn't have many relations back to his family, now that they were gone. He hoped that this could go part of the way to honouring their memory. "Could you do that with the Shinto Gods, Susanoo, Ameterasu and Tsukiyomi? Each of them, with eyes and have a large Uchiha fan in the middle to link it all together?"

Had Sasuke known how much effort that went into something like that, he may have felt bad asking for that much. Meanwhile, Jiraiya rolled his eyes, knowing how long that something like that, done to his standards would take.

_This kid better be worth it Sensei. _Jiraiya thought to himself. Whilst Sasuke had no idea what he was doing, the silver haired man was creating leverage to then get Sasuke to actively do the conditions in their agreement.

The idea would be to create a feedback loop that was beneficial to Konoha. With Sasuke getting power, quicker and with better training, the more that he created bonds in the village and helped out his comrades.

It was the same tactics the Inuzuka family would use to train their dogs, just a slightly larger scale. From the reports that he had gotten from his sensei and the village at large, this kid needed drastic intervention as he was becoming a serious concern of being flight risk.

**x-X-x**

8 hours. 8 hours is how long it took but when looking in the mirror, Sasuke grinned even harder than when he activated his sharingan. The work done on his back look really cool in his opinion. It was a full back piece that went from his lower spine to his upper traps and trailed off where his arms met his shoulders.

The great thing that Jiraiya had done for Sasuke, which was really for the next plan that Jiraiya had was he used medical ninjutsu as he was going along to speed up the healing process. By what the Sannin had said, the tattoo would be fully healed within a couple of days, far quicker than if it was done via civilian methods.

"Kid, now you have to hold up one of the conditions. You're going to need to have experience having sex if you want to be able to critique my stories."

"What!?" Sasuke blurted out, a massive blush on his face.

Jiraiya quickly clarified. "NOT WITH ME. We're going to go somewhere and I'll pay for it." Now Sasuke was never concerned with the idea of love and that your first time should be with someone you care about but the idea of having to pay for it didn't sit well with him, even if he didn't fully know what he was getting into.

_I'm doing this so I can get the power to kill Itachi. I'm doing this so I can get the power to kill Itachi. I'm doing this so I can get the power to kill Itachi. _Sasuke repeated over and over in his mind to justify what he was about to agree to.

"Okay fine. I don't want anyone knowing it is me though. I'm not going to negotiate on that." The last thing that the uchiha heir wanted, was for this to get out to the public. The Uchiha and Sasuke by association cared heavily about their appearance and the perception of the clan due to it's standing as a founding clan of Konoha.

"I knew you would say that. Here's a seal that when activated, will henge you into someone else for as much chakra you put in it. You can cancel it at any time."

After applying the seal, which thankfully was temporary and did not mar his skin, Sasuke stepped out of the house along side Jiraiya, looking like a teenager with long brown hair, green eyes and a bit of stubble.

A shunshin was used by Jiraiya to teleport them into the brothel. Jiraiya did all the talking whilst Sasuke blushed in complete embarrassment. His face was as red as his favourite fruit.

There in front of him, were numerous girls, ranging from various states of undress, some being completely naked. They were all sorts of shapes, sizes and age. His head was moving quickly and a few of the girls that he locked eyes with unintentionally gave him a smirk of giggled at him, obviously noticing his experience or lack there of.

"Oi brat, choose who you want your first time to be with." Sasuke suddenly realised that all of the attention was on him now and he actually had to pick. He had no idea what to go for, there were so many to choose from!

In the end he settled for a girl who had died blonde hair, the slightest hint of abs, curvy hips that were quite sizeable. She was wearing a white robe which had pink floral accents, decorating the "That one Jiraiya-sensei" the raven haired Uchiha mumbled whilst pointing her out. For her part, she smiled gracefully as Jiraiya grinned with glee.

He would have hated it if he had to pick for Sasuke. This at least showed he had an interest in women. From what he had heard, the boy had all of the girls at the academy flocking over him and did nothing about it.

"Come this way darling, I'm confident that we're going to have a great time." She smiled as she spoke and Sasuke looked at Jiraiya, before taking a deep breath, then he walked towards the fine lady.

A proud smirk was on the face of Jiraiya as he watched his young protege. A few seconds later, Jiraiya looked at the other girls talking amongst one another and found a girl who looked very similar to a former teammate of his. He knew who he was sleeping with tonight as he pushed the pain in his heart to the back of his mind,

**x-X-x**

Half an hour later and Sasuke was quick to leave, making sure that the henge that was on him was in place and left without telling Jiraiya. There was a large blush marring the cheeks of Sasuke but strangely, at least in the perspective of Sasuke, he actually kind of felt good. Really good. There was not as much internal stress placed on his shoulders. He felt far more relaxed and the orgasm he had made him feel really good.

Suddenly, Sasuke realised just what the big deal with sex was. He now knew what people enjoyed it. Touching breasts, kissing, being inside a woman. These were all new sensations that he liked. It wasn't all just good feelings though. Sasuke realised that he had areas to improve. It was his first time after all, but being told "to not worry about her pleasure" told Sasuke that he wasn't good at making the other person feel good, due to his inferiority complex.

It was not lost on the Uchiha heir that sooner, rather than later, he would want to start having sex with girls that were not being paid to do it. If word got out that he was only sleeping with people that were paid, it would destroy the reputation of the Uchiha clan and that was simply not acceptable.

_Maybe this training from Jiraiya won't be so bad if I 'have' to keep having sex, especially if he is paying for it._

* * *

**Author's Notes: And there you have it. Hopefully this is a different spin on the whole "good Sasuke". This will have mature themes and if you have any suggestions for the story, please let me know and giving the story a review would mean a lot!**


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